Trifluoroacetic acid → HCID 178484181、化合物

HRID 1919170ノート

反応式

HRID 1919170 の反応式
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26].[NH:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]1[NH:38][C:39]([C:42]2[S:43][C:44]([C:47]3[S:51][C:50]([C:52]4[NH:56][C:55]([C@@H:57]5[CH2:61][CH2:60][CH2:59][NH:58]5)=[N:54][CH:53]=4)=[N:49][CH:48]=3)=[CH:45][N:46]=2)=[CH:40][N:41]=1.Cl.[CH3:63][N:64]([CH3:75])[C@H:65]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:66](O)=[O:67].C[CH2:77][N:78]([CH:82]([CH3:84])[CH3:83])[CH:79](C)C>CN(C)C=O.CO.O>[F:28][C:27]([F:30])([F:29])[C:25]([O-:31])=[O:26].[S:43]1[C:44]([C:47]2[S:51][C:50]([C:52]3[N:56]=[C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:83](=[O:26])[C@@H:82]([C:84]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:78]([CH3:77])[CH3:79])[NH:54][CH:53]=3)=[N:49][CH:48]=2)=[CH:45][N:46]=[C:42]1[C:39]1[N:38]=[C:37]([C@@H:33]2[CH2:34][CH2:35][CH2:36][N:32]2[C:66](=[O:67])[C@@H:65]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[N:64]([CH3:75])[CH3:63])[NH:41][CH:40]=1

参加物

10

反応物 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45835119(R)-a-(Dimethylamino)benzeneacetic acid HClHCID 53233526HCID 53233526、化合物

生成物 2

HCID 84468TrifluoroacetateHCID 178484181HCID 178484181、化合物収率 34%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

HATU (66 mg, 0.17 mmol) was added to a stirred solution of a TFA salt of 2,2′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-5-yl)-5,5′-bi-1,3-thiazole (40 mg, 0.045 mmol), (R)-2-(dimethylamino)-2-phenylacetic acid hydrochloride (39 mg, 0.18 mmol) and DIEA (0.078 mL, 0.45 mmol) in dimethylformamide (2 mL) at room temperature. The reaction was stirred for 3 h, diluted with methanol (2 mL) and water (2 mL) and stirred for 15 min. The reaction mixture was concentrated in vacuo to dryness and purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u, eluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA). Fractions containing the desired product were concentrated to yield a trifluoroacetate salt of (1R,1′R)-2,2′-(5,5′-Bi-1,3-thiazole-2,2′-diylbis(1H-imidazole-4,2-diyl(2S)-2,1-pyrrolidinediyl))bis(N,N-dimethyl-2-oxo-1-phenylethanamine) (18 mg, 0.015 mmol, 34% yield) as an orange solid.

後処理

  1. stirringstirred for 15 min
  2. concentrationThe reaction mixture was concentrated in vacuo to dryness
  3. custompurified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u
  4. washeluted with a gradient of 10 to 80% acetonitrile/water/0.1% TFA)
  5. additionFractions containing the desired product
  6. concentrationwere concentrated

出典と根拠

ORDレコード
ord-0c5fe72377ee41a6a1b80e06c60bf77c
出典データセット
uspto-grants-2013_12
特許番号
US08618153B2

反応ノート

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